From amazing individual milestones to events that changed hockey forever, the Canadiens' history is full of unforgettable occasions. Some of these moments delighted fans, others enraged them and a few were downright tragic.

Here are the top five moments in the history of the Montreal Canadiens.

Honorable Mentions

The Montreal Canadiens run in the 1993 Stanley Cup playoffs was magical, winning an unprecedented 10-straight overtime games before finally beating the Wayne Gretzky-led Los Angeles Kings in five games.

During the spring of 1993, the Canadiens won seven games in extended time just to get to the Stanley Cup finals. After dropping the first game of the finals, Games 2 through 4 were all tied after regulation.

Eric Desjardins was the hero in Game 2, scoring the tying goal with the net empty, and the OT game-winner just 51 seconds after the puck dropped in the fourth period.

Then in Games 3 and 4, a young John Leclair would make himself known to the hockey world by scoring the game winners on both nights.

Leclair's second OT goal in as many games on June 7, 1993 gave the Canadiens their 10th straight overtime win, and they headed back to Montreal with a commanding three games to one lead.

Two nights later, the Habs would win their 24th Stanley Cup.

Howie Morenz's Funeral

Date: March 10, 1937.

Howie Morenz was one of hockey's brightest stars at the time, a goal-scorer the game had not seen to date. He was loved by Canadiens fans, and his tragic death following a gruesome on-ice injury led to one of the most memorable moments in Canadiens' history.

5. Maurice Richard's 50 in 50

Maurice Richard entered the 50th and final game of the 1944-45 season with 49 goals. No player in the history of the game had yet scored 50. After having a goal disallowed the previous evening, The Rocket was determined to reach the milestone against the Boston Bruins.

The Bruins played a tight checking game, not wanting to have any part in Richard's quest. They managed to keep Richard goalless through 57 minutes. But with 2:15 left in the third period, Richard took a pass from Elmer Lach, fired it past Bruins goaltender Harvey Bennett and made history.

Maurice Richard was not only the first player in NHL history to score 50 goals, but he did it in just 50 games as well.

4. The Mask

Jacques Plante was a hockey visionary. He is credited as being the first goalie to stop the puck behind the net for his defensemen. He was the first to raise his arm on icing calls so his defenders knew what was happening behind them. His stand-up style of goalkeeping would be imitated by others for years to come.

Plante revolutionized the game in many ways, but what happened at Madison Square Garden on November 1, 1959, would change the game forever.

Three minutes into the game, New York Rangers forward Andy Bathgate let go a backhand shot that caught Plante on the left side of his face, just below the eye. As blood dripped down his face, the Montreal Canadiens star goaltender returned to the locker room for repairs.

This was a common occurrence in the pre-mask era. The game was paused, goalies were sewn up by the arena doctor, the netminder returned to the ice and the puck was dropped again.

The delay on November 1, 1959, however was longer than usual. Jacques Plante had taken one too many pucks to the face. He would not simply get stitched up and return. Not on this evening. Not unless he could wear a mask.

Montreal's coach Toe Blake would not hear of it. Two points were on the line, and he did not want his goalie's vision to be obstructed by a piece of fiberglass. Blake was missing a key bargaining chip, however. The Montreal Canadiens did not have a backup goaltender.

And so hockey history was made. Plante returned to the ice, wearing his mask in a game for the first time. He carried a shutout into the third period, eventually allowing a lone goal as the Canadiens beat the Rangers 3-1.

3. Roy Demands a Trade

Patrick Roy was the king of Montreal. The 30-year-old goaltender had already led the Canadiens to two Stanley Cups—one as a rookie in 1986 where he became the youngest ever Conn Smythe winner, and one in 1993 where he won a record 10-straight overtime games.

He was well on his way to rewriting the record books and going down in history as the next great Canadiens' goaltender. Until Mario Tremblay was hired as head coach, that is.

Roy and Tremblay had a rocky relationship before the events in December of 1995. The two would often get into arguments at practice, their animosity for each other likely stemming from Tremblay's criticism of Roy while working on a sports-talk radio show.

But on this fateful night at the Montreal Forum, their relationship boiled over. The Detroit Red Wings were in town and came flying out of the gates, scoring five goals in the first period. Usually this is enough for a coach to give his No. 1 goalie the rest of the night off.

Tremblay had other plans and Roy was sent back on the ice for the second period. He wound up letting in four more goals before Tremblay finally replaced him. Roy was livid. He felt Tremblay had left him in the goal to purposely embarrass him. The goaltender got off the ice, removed his mask and went directly to president Ronald Corey to deliver a clear message: He had played his last game as a member of the Montreal Canadiens.

Four days later, rookie general manager Rejean Houle traded Roy and captain Mike Keane to the Colorado Avalance for Andrei Kovalenko, Martin Rucinsky and Jocelyn Thibault. It is often considered as one of the worst trades in NHL history.

Roy would win two more Cups with the Avalanche and retire with more wins than any other goalie in NHL history.

2. Five Straight Stanley Cups

The Montreal Canadiens had won 11 Stanley Cups prior to 1960, including the previous four. No team in NHL history had won five straight.

The Canadiens entered the postseason semifinals against Chicago, and disposed of the Blackhawks in four games. Next up were the Toronto Maple Leafs, desperate to put an end to The Flying Frenchmen's dominance over the NHL.

The Leafs proved no match, however, as the Habs rolled to wins in the first three games of the series. Game 4 was to be played at Maple Leaf Gardens on April 14, 1960.

1. The Richard Riot

Maurice Richard's name will always be synonymous with goal-scoring, but the The Rocket had a mean streak as well.

After taking a stick to the face against the Boston Bruins on March 13, 1955, Richard went after Bruins' defenceman Hal Laycroe. Linesman Cliff Thompson tried to stop Richard, and, as the two fell to the ground, Richard struck Thompson with his fist.

Campbell was a gutsy man and he turned up at the Montreal Forum just three days after incident that led to Richard's suspension. Tensions ran high. Canadiens fans were completely disinterested in the game being played, instead focusing their efforts on verbally abusing Campbell and hurling objects in his direction.

After the first period ended, things reached a tipping point when a tear gas bomb exploded inside the Forum. The arena was evacuated and the game forfeited.

The thousands at the game took to the streets as thousands more joined, rioting in protest. The chaos ensued through the evening, eventually subsiding after The Rocket himself took to the radio to plead with the public to end the madness.